2,8-dibromo-5,11-dihexyl-6,12-diphenyl-5,11-dihydroindolo[3,2-b]carbazole | 1352420-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,8-dibromo-5,11-dihexyl-6,12-diphenyl-5,11-dihydroindolo[3,2-b]carbazole
• 英文别名: 2,8-Dibromo-5,11-dihexyl-6,12-diphenylindolo[3,2-b]carbazole
• CAS: 1352420-74-6
• 化学式: C₄₂H₄₂Br₂N₂
• 分子量: 734.617
• InChiKey: NDBVUCBRTRNJHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,8-dibromo-5,11-dihexyl-6,12-diphenyl-5,11-dihydroindolo[3,2-b]carbazole 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成 2,8-bis(2-phenylethenyl)-5,11-dihexyl-6,12-diphenyl-5,11-dihydroindolo[3,2-b]carbazole
  参考文献：
  名称：

  新型2,8-二取代的吲哚[3,2- b ]咔唑的合成†

  摘要：

  研究了一个新的合成途径，向2,8-双官能化的吲哚[3,2- b ]咔唑。提出的方法提供了一条短而高产的途径2,8-二溴-5,11-二己基-6,12-二苯基-吲哚[3,2- b ]咔唑。结果表明，后者是一种通用的结构单元，能够使用中等至良好的收率合成许多以前未报道的5,11-二烷基-6,12-二苯基-吲哚并[3,2- b ]咔唑铃木和Sonogashira的交叉偶联反应。此外，它表明2,8-二溴-5,11-二己基-6,12-二苯基-吲哚[3,2- b ]咔唑可以容易地甲酰化，从而产生2,8-二甲酰基-5,11-二己基-6,12-二苯基-吲哚-[3,2- b ]咔唑。后一种化合物成功地进行了缩合反应。

  DOI：

  10.1039/c1ob06298k
• 作为产物：
  描述：

  5,11-dihexyl-6,12-diphenyl-5,11-dihydroindolo[3,2-b]carbazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 6.0h， 以68%的产率得到2,8-dibromo-5,11-dihexyl-6,12-diphenyl-5,11-dihydroindolo[3,2-b]carbazole
  参考文献：
  名称：

  A novel D-A-D-A-D type molecule based on substituted dihydroindolo [3, 2-b] carbazole with large two-photon absorption cross section and excellent aggregation-induced enhanced emission property

  摘要：

  Two novel D-A-D-A-D type molecules T1 and T2 based on substituted dihydroindolo [3, 2-b] carbazole with large two-photon absorption (2PA) cross section and excellent aggregation-induced enhanced emission (AIEE) property have been synthesized and characterized. Both compounds emit weakly fluorescent in THF, while a significant AIEE property is observed in water/THF (v/v 50%/50%) for T1 and water/THF (v/v 90%/10%) for T2 with a sharp increase in fluorescence intensity. The solid fluorescence of T1 and T2 is located at 575 nm and 588 nm, and their quantum efficiencies are determined to be 3.2% and 5.8%, respectively. The corresponding 2PA cross section values for T1 and T2 at 800 nm are 867 GM and 1300 GM by the open-aperture Z-scan technique. These excellent performances of both compounds make them as attractive alternatives for biophotonic and optoelectronic applications. (C) 2015 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2015.11.047

文献信息

• Synthesis of novel 2,8-disubstituted indolo[3,2-b]carbazoles
  作者：Sven Van Snick、Wim Dehaen

  DOI：10.1039/c1ob06298k

  日期：——

  2,8-difunctionalised indolo[3,2-b]carbazoles was investigated. The presented method offers a short and high yielding route towards 2,8-dibromo-5,11-dihexyl-6,12-diphenyl-indolo[3,2-b]carbazole. It is demonstrated that the latter compound is a versatile building block, enabling the synthesis of a number of previously unreported 5,11-dialkyl-6,12-diphenyl-indolo[3,2-b]carbazoles in moderate to good yields

  研究了一个新的合成途径，向2,8-双官能化的吲哚[3,2- b ]咔唑。提出的方法提供了一条短而高产的途径2,8-二溴-5,11-二己基-6,12-二苯基-吲哚[3,2- b ]咔唑。结果表明，后者是一种通用的结构单元，能够使用中等至良好的收率合成许多以前未报道的5,11-二烷基-6,12-二苯基-吲哚并[3,2- b ]咔唑铃木和Sonogashira的交叉偶联反应。此外，它表明2,8-二溴-5,11-二己基-6,12-二苯基-吲哚[3,2- b ]咔唑可以容易地甲酰化，从而产生2,8-二甲酰基-5,11-二己基-6,12-二苯基-吲哚-[3,2- b ]咔唑。后一种化合物成功地进行了缩合反应。
• A novel D-A-D-A-D type molecule based on substituted dihydroindolo [3, 2-b] carbazole with large two-photon absorption cross section and excellent aggregation-induced enhanced emission property
  作者：Guojian Tian、Ning Xiang、Haitao Zhou、Yiru Li、Bo Li、Qiaochun Wang、Jianhua Su

  DOI：10.1016/j.tet.2015.11.047

  日期：2016.1

  Two novel D-A-D-A-D type molecules T1 and T2 based on substituted dihydroindolo [3, 2-b] carbazole with large two-photon absorption (2PA) cross section and excellent aggregation-induced enhanced emission (AIEE) property have been synthesized and characterized. Both compounds emit weakly fluorescent in THF, while a significant AIEE property is observed in water/THF (v/v 50%/50%) for T1 and water/THF (v/v 90%/10%) for T2 with a sharp increase in fluorescence intensity. The solid fluorescence of T1 and T2 is located at 575 nm and 588 nm, and their quantum efficiencies are determined to be 3.2% and 5.8%, respectively. The corresponding 2PA cross section values for T1 and T2 at 800 nm are 867 GM and 1300 GM by the open-aperture Z-scan technique. These excellent performances of both compounds make them as attractive alternatives for biophotonic and optoelectronic applications. (C) 2015 Published by Elsevier Ltd.